5-Chloro-2-hydroxy-3-methylbenzaldehyde → 1-(6-chloro-8-methyl-2H-chromen-3-yl)ethan-1-one

Reaction equation

[OH:1][C:2]1[C:9](C)=CC(C)=C[C:3]=1[CH:4]=O.[OH:12][C:13]1[C:20]([CH3:21])=[CH:19][C:18]([Cl:22])=[CH:17][C:14]=1[CH:15]=O>>[Cl:22][C:18]1[CH:17]=[C:14]2[C:13](=[C:20]([CH3:21])[CH:19]=1)[O:12][CH2:4][C:3]([C:2](=[O:1])[CH3:9])=[CH:15]2

Participants

Reactant 2

HCID 27743585-Chloro-2-hydroxy-3-methylbenzaldehyde

HCID 47702452-Hydroxy-3,5-dimethylbenzaldehyde

Product 1

HCID 144791201-(6-chloro-8-methyl-2H-chromen-3-yl)ethan-1-one

Procedure

Using the procedure described in Example 1, stage A, but with 2-hydroxy-3,5-dimethylbenzaldehyde replaced by 2-hydroxy-3-methyl-5-chlorobenzaldehyde, the expected product is obtained, and this is purified by an additional recrystallization in an isopropyl ether/petroleum ether mixture.

Sources & evidence

ORD record: ord-65e682ada16044d38622735a98eb2d76
Source dataset: uspto-grants-1990_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04975454

Reaction notes

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